Oakland Trails
Homes for Sale in Oakland, FL
All 37 homes for sale in Oakland, FL · median $796,000 · 24 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-20, 9 recorded sales closed at a median of $537,000, $223 per square foot, a median 112 days on market, sellers accepting 90% of original asking (-2% versus the prior year). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,950 ($8,280 with the full homestead exemption).
| Location | Oakland, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 329 (FL DOR 2025 assessment roll) |
| Years built | 2017–2020 (median 2018.0) |
| Typical living area | 2,082 sq ft (median) |
| Sale prices, last 12 months | $537,000 median across 9 closed sales · $223 per sq ft · -1.5% vs the prior 12 months |
| Days on market (closed sales) | 112 median |
| Owner-occupied (homestead) share | 72% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2018 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Oakland Trls Ph 2 key facts,” movewithmomentum.com/neighborhoods/oakland-trls-ph-2, data as of September 20, 2026.
Oakland Trails right now
🟡 Off the recent peak. The trailing-12-month median ($537K) is down 1.5% from the prior 12 months ($545K). With about 7 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Medium (9 and 11 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 5, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside Oakland TrailsHomes for Sale in Oakland, FL right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Oakland Trails market snapshot (as of September 20, 2026): the median sale price is about $537K ($223 per sq ft over the trailing 12 months of closed sales), and a median 112 days on market for closed sales. The trailing-12-month median is down 2% from the prior 12 months, computed from record-level Stellar MLS closed sales (9 closings in the current window).
In ZIP 34787 (Oakland), 2,147 homes closed in the last 12 months at a median of $598K ($252/sq ft), down 0.8% year over year, with a median 36 days on market. Right now 352 active and 181 pending listings put supply at about 3.7 months — a balanced market. See the live ZIP 34787 housing market and the Orange County market.
County records show 37 qualified sales in Oakland Trails across 2024–2025 (23 in 2024, 14 in 2025), median $512,500 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Oakland Trails is a community of 329 homes in Oakland, Orange County, built between 2017 and 2020 (median 2018.0), with a median living area of about 2,082 square feet. 72% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($537K) IS the median in the snapshot above, and the move from 2025 ($545K) IS the -1.5% one-year change.
Windows contain 0 to 17 sales each (9 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2018 through 2026. Deemed reliable but not guaranteed.
29% of homes for sale in ZIP 34787 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-20).
Housing distress & ownership in Oakland Trls Ph 2, Oakland
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Recent Developments in Oakland Trls Ph 2
Development, infrastructure, retail, and school activity affecting Oakland Trls Ph 2, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated August 2026.
- July 2026Development
Capstone begins construction on The Gateway luxury apartments
Capstone Building Corp began construction on The Gateway, a 270-unit apartment community at 7250 Shadowridge Drive in Orlando, developed by JBL Development. The five-story gated project spans more than 417,000 square feet and is expected to be completed in late 2027. Amenities include a saltwater pool, fitness center, pickleball court, and a clubhouse with a restaurant and bar.
What it may mean for the marketAdds 270 market rate apartments in a five story building with resort style amenities, expanding the local rental housing stock in the Airport Lakes area of south Orlando. The project is about 21 miles southeast of Oakland Trls Ph 2, elsewhere in Orange County.
Source: Construction Owners - July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The project is about 17 miles south of Oakland Trls Ph 2, elsewhere in Orange County.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 11 miles south of Oakland Trls Ph 2, elsewhere in Orange County.
Source: Orange County Newsroom - June 2026Development
Mixed-use high-rise redesigned for 924 and 934 North Magnolia Avenue
A redesigned 17-story mixed-use high-rise was proposed for 924 and 934 North Magnolia Avenue in Orlando's North Quarter district by Acram Group. The project would include 350 residential units, about 3,300 square feet of ground-floor commercial space, and a parking garage with 510 spaces, replacing two 1972 office buildings. A public plaza is planned at the corner of Magnolia and Weber Street.
What it may mean for the marketWould replace two aging office buildings with 350 residences, ground floor retail, and structured parking, adding housing density and a public plaza along the Orlando Urban Trail. The project is about 13 miles southeast of Oakland Trls Ph 2, elsewhere in Orange County.
Source: Florida YIMBY - June 2026Development
Planning board approves zoning for 37-story tower at 170 East Washington Street
Orlando's Municipal Planning Board voted to approve a Planned Development amendment for a 37-story, 425-foot mixed-use tower at 170 East Washington Street across from Lake Eola Park. The project would include 252 residential units, a 221-room hotel, a three-story restaurant, and structured parking. It still requires City Council consideration before construction.
What it may mean for the marketWould add a 37 story tower with 252 residences and a hotel to the downtown skyline, replacing a prior approval for a 7 story hotel and increasing high density housing and parking supply. The project is about 13 miles southeast of Oakland Trls Ph 2, elsewhere in Orange County.
Source: Florida YIMBY - October 2025Retail & Dining
New Apopka complex with restaurants and offices set to open in 2026
A new commercial complex in Apopka with restaurants and office space is set to open in 2026, adding retail and workplace space in northwest metro Orlando.
What it may mean for the marketNew retail and office space in Apopka adds everyday conveniences and local jobs, amenity and employment factors that can support nearby housing demand. The site is about 4 miles southwest of Oakland Trls Ph 2.
Source: GrowthSpotter
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
The Oakland Trails buying strategy.
If we were buying in Oakland Trails today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Oakland Trails.
A closer look at the Oakland Trails market
At a median of $223 per square foot, Oakland Trails prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The trailing-12-month median down 2% year over year. Homes that do trade take a median 112 days on market, useful leverage on any listing that has lingered.
The housing stock is 329 homes built between 2017 and 2020, and 72% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Oakland Trails. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Oakland Trails buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (5.4). Basis: Recent Direction -1.5% year-over-year; Owner Commitment 72% owner-occupied; Pricing Power 90.2% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Oakland Trails buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Oakland Trails sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Oakland Trails, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Oakland Trails home worth?
Get a no-obligation home value based on real comparable sales in Oakland Trails, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Oakland →
Frequently Asked Questions
What is the median home price in Oakland Trails?
How long do homes in Oakland Trails take to sell?
How many homes are in Oakland Trails?
What share of Oakland Trails is owner-occupied?
When were the homes in Oakland Trails built?
Who is the best real estate agent for Oakland Trails?
How do I find a top Oakland real estate agent who knows Oakland Trails?
Can Momentum Realty connect me with an agent for Oakland Trails?
Where is Oakland Trails, and what county is it in?
Is Oakland Trails a good place to live?
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2018 (62 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Oakland Trls Ph 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Oakland Trails with Momentum Realty’s local guides.